US7427643B2 - Polymeric film or coating comprising hemicellulose - Google Patents

Polymeric film or coating comprising hemicellulose Download PDF

Info

Publication number
US7427643B2
US7427643B2 US10/548,799 US54879905A US7427643B2 US 7427643 B2 US7427643 B2 US 7427643B2 US 54879905 A US54879905 A US 54879905A US 7427643 B2 US7427643 B2 US 7427643B2
Authority
US
United States
Prior art keywords
film
hemicellulose
food
packaging material
coating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime, expires
Application number
US10/548,799
Other languages
English (en)
Other versions
US20060173104A1 (en
Inventor
Paul Gatenholm
Aase Bodin
Maria Gröndahl
Sofia Dammstrom
Lisa Eriksson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Seelution AB
Original Assignee
Xylophane AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20290761&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US7427643(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Xylophane AB filed Critical Xylophane AB
Assigned to XYLOPHANE AKTIEBOLAG reassignment XYLOPHANE AKTIEBOLAG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ERICKSSON, LISA, BODIN, AASE, GATENHOLM, PAUL, DAMMSTROM, SOFIA, GRONDAHL, MARIA
Publication of US20060173104A1 publication Critical patent/US20060173104A1/en
Application granted granted Critical
Publication of US7427643B2 publication Critical patent/US7427643B2/en
Assigned to XYLOPHANE AB reassignment XYLOPHANE AB CHANGE OF ADDRESS Assignors: XYLOPHANE AB
Assigned to SEELUTION AB reassignment SEELUTION AB ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: XYLOPHANE AB
Adjusted expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/14—Hemicellulose; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/14—Hemicellulose; Derivatives thereof

Definitions

  • the present invention relates to a film-forming composition and a polymeric film or coating comprising hemicellulose. It also relates to the use of said film or coating as an oxygen barrier. Further, the invention relates to a method for the manufacture of a polymeric film or coating comprising hemicellulose, as well as to a method for improving the film-forming properties of hemicellulose.
  • EVOH Ethylene vinyl alcohol
  • PVOH polyvinyl alcohol
  • Hemicelluloses are polysaccharides that are biosynthesized in the majority of plants, where they act as a matrix material present between the cellulose microfibrils and as a linkage between lignin and cellulose. Hemicelluloses have been commercially used as sweetening agents, thickeners and emulsifiers in food. So far the non-food utilisation of hemicelluloses has been very limited. For example they have not yet been used commercially for the preparation of polymeric materials.
  • hemicellulose exhibit poor film-forming properties resulting in either fragmented or very brittle films.
  • the film-forming properties vary with the structure of the hemicellulose, which in turn is varying depending on its natural source and the extraction method. To be appropriate as a barrier material the film-forming properties have to be improved.
  • WO 02/06411 the use of heteroxylans for the preparation of a film-forming composition containing a plant protectant is disclosed.
  • the aim of WO 02/06411 is to provide a composition which is useful for applying a plant protectant to seeds or agricultural products.
  • the purpose of incorporating heteroxylans is to obtain a film-forming composition for the application of the plant protectant.
  • the molecular weight of the heteroxylans used in WO 02/06411 ranges from 100 000 to 250 000 g/mol.
  • the use of high molecular weight hemicellulose produces compositions having relatively high viscosities, which makes the compositions difficult to handle practically.
  • a biodegradable film is obtained by subjecting water-soluble hemicellulose to film-formation.
  • the hemicellulose used has an average molecular weight in the range of 50 000 to 1 000 000, preferably in the range of 100 000 to 400 000. Again, the high molecular weights present handling problems due to high viscosity.
  • the thickness of the films described in U.S. Pat. No 6,004,616 is 0,1 mm in dried state.
  • the films are relatively thick, which requires a lot of material to be consumed in the manufacture of the films. As a consequence thereof, the cost of materials will be very high.
  • an object of the present invention is to provide flexible films or coatings based on hemicellulose having a molecular weight of 50 000 g/mol or less.
  • Another object is to provide a film-forming composition and films or coatings based on hemicellulose having a molecular weight of 50 000 g/mol or less, which can be used as oxygen barriers.
  • hemicellulose having a molecular weight of 50 000 g/mol or less with at least one component selected from the group consisting of plasticizers, cellulose and an oligomer or polymer, and forming a film or coating thereof.
  • the polymeric film or coating thereby formed can be used as an oxygen barrier.
  • hemicellulose having a molecular weight of 50 000 or less is advantageous because it allows for a greater number of hemicellulose raw material to be used for the preparation of films or coatings. Further, there are more extraction methods available for extracting molecules having lower molecular weights.
  • One further advantage with the present invention is the excellent oxygen barrier properties of the films or coatings produced.
  • the measured oxygen permeability was in the same range as for the commercially used barrier EVOH and for films of starch.
  • Another advantage of the present invention is that the mechanical properties of the films or coatings produced can be controlled by addition of various amounts or types of plasticizers, cellulose or blending with other polymers or oligomers.
  • a further advantage is that the raw material in the present invention is renewable and can be extracted from biomass.
  • Hemicelluloses are substituted/branched polymers of low to high molecular weight. They consist of different sugar units arranged in different portions and with different substituents. Pentosan-rich polysaccharides have a prevalent pentose content and constitute the largest group of hemicelluloses.
  • a “pentosan-rich polysaccharide” refers to a polysaccharide having a pentosan content of at least 20% by weight, and a xylose content of at least 20% by weight; for example, the polysaccharide has a pentosan content of 40% to 80% by weight, and a xylose content of 40% to 75% by weight.
  • Pentosan-rich polysaccharides in particular xylans, are the most preferred compounds for use according to the present invention, since they are not so sensitive to humidity.
  • hemicelluloses may be used according to the invention, e.g. glucomannan, galactoglucomannan or arabinogalactan.
  • Hemicellulose, in particular xylans, for use according to the invention have a molecular weight of less than 50 000 g/mol.
  • the hemicellulose has a molecular weight greater than 8 000 g/mol.
  • the hemicellulose may have a molecular weight in the range of 8 000-50 000 g/mol, 8 000-48 000 g/mol or 8 000-45 000 g/mol.
  • molecular weights of the hemicellulose are 8 000-15 000 g/mol, 8 000-14 000 g/mol, 8 000-13 000 g/mol, 8 000-12 000 g/mol, or in particular 8 000-11 000 g/mol.
  • the use of low molecular weights is an advantage as hemicellulose from many sources can be used and the extraction procedure is simplified.
  • molecular weights of the hemicellulose are 15 000-50 000 g/mol, 20 000-50 000 g/mol, 15 000-48 000 g/mol, 20 000-48 000 g/mol, 15 000-45 000 g/mol, or in particular 20 000-45 000 g/mol or 20 000-40 000 g/mol.
  • the use of somewhat higher molecular weights facilitates film formation. If even higher molecular weights are used, high viscosity can complicate the use of the hemicellulose to produce a film or coating and the extraction methods are considerably restricted.
  • Xylans are present in biomass such as wood, cereals, grass and herbs and they are considered to be the second most abundant biopolymer in the plant kingdom. To separate xylans from other components in various sources of biomass, extraction with water and aqueous alkali can be used. Xylans are also commercially available from sources as Sigma Chemical Company.
  • Xylans may be divided into the sub-groups of heteroxylans and homoxylans.
  • the chemical structure of homoxylans and heteroxylans differs.
  • Homoxylans have a backbone of xylose residues and have some glucuronic acid or 4-O-methyl-glucuronic acid substituents.
  • Heteroxylans also have a backbone of xylose residues, but are in contrast to homoxylans extensively substituted not only with glucuronic acid or 4-O-methyl-glucuronic acid substituents but also with arabinose residues.
  • An advantage of homoxylans compaired to heteroxylans is that homoxylans crystallize to a higher extent. Crystallinity both decreases gas permeability and moisture sensitivity.
  • homoxylan which can be used according to the invention is glucuronoxylan.
  • heteroxylans which can be used according to the invention are arabinoxylan, glucuronoarabinoxylan and arabinoglucuronoxylan.
  • Xylans from any biomass or commercial source may be used to produce the films or coatings in the present invention.
  • film-formation is a necessary recruitment.
  • a film-forming composition of hemicellulose, in particular xylans may be achieved by various strategies.
  • One way to do this is to add low molecular weight plasticizers.
  • Another way to prepare coherent films is to add finely divided cellulose.
  • a third procedure to obtain films is by blending xylan with other oligomers or polymers.
  • An additional strategy to achieve better film-forming properties is to mix hemicelluloses of different molecular weights or structures. It is also possible to use a combination of one or more of the before mentioned strategies.
  • the films or coatings may be prepared by casting of an aqueous solution or dispersion of the pentosane-rich polysaccharide.
  • aqueous solution or dispersion of the pentosane-rich polysaccharide Although other solvents could be used as solvents in the present invention, water is the most preferred solvent.
  • film refers to a separate sheet, which can be used e.g. for the packaging of food or pharmaceuticals.
  • coating refers to a covering that can be integrated in e.g. a carton in order to provide an oxygen barrier layer.
  • the film or coating according to the invention may have a thickness of 100 micrometers or less.
  • the film or coating may have a thickness of 50 micrometers or less, or more specifically the film or coating may have a thickness of 10 micrometers or less.
  • the film or coating may have a thickness of 2 micrometers or 1 micrometer and still present the desired properties.
  • plasticizer as used herein relates to a substance of low molecular weight, which increases the flexibility of the material.
  • plasticizers that may be used are water, sugars such as glycerol, xylitol, sorbitol and maltitol, ethylene glycol, propylene glycol, butanediol, glycerine and urea.
  • the content of plasticizer is in the range of 1-60% by dry weight, e.g. in the range of 20-50% by dry weight.
  • the cellulose added to improve the film-forming properties can originate from any biomass such as cotton, wood and agriculture residues or commercial source or be produced by bacteria.
  • the cellulose is finely divided.
  • the content of finely divided cellulose is in the range of 1-90% by dry weight, e.g. in the range of 50-75% by dry weight.
  • the polymer or oligomer added can be of any type.
  • the polymer or oligomer added to obtain a coherent film is polyvinyl alcohol of various molecular weights.
  • the content of polymer or oligomer is in the range of 1-90% by dry weight, e.g. in the range of 20-75% by dry weight.
  • oxygen barrier used throughout this application is meant a material, which has low permeability to oxygen.
  • the oxygen barrier can be used to protect a substance, e.g. food or medicals, from exposure to oxygen.
  • the polymeric films or coatings according to the present invention can be used as an oxygen barrier in food packaging or pharmaceutical packaging.
  • films or coatings of the present invention can be used as an oxygen barrier layer on e.g. cartons and paper, possibly in combination with a water resistant material.
  • the films or coatings of the present invention can also be used for drug delivery, edible films and other polymeric applications.
  • This example illustrates the production of a film based on xylan, where the film-forming properties have been improved using the low molecular plasticizer xylitol.
  • a series of films containing 20%, 27.5%, 35%, 42.5% and 50% of added xylitol (dry weight) were investigated.
  • a mixture of xylitol and glucoronoxylan from aspen with a total weight 1 g was solubilized in 35 ml of water in 95° C. for 15 minutes. The solution was then poured onto polystyrene Petri dishes with a diameter of 14 cm. After drying in 23° C. and 50% RH for two to three days, transparent and more or less flexible films were obtained.
  • the molar mass of the glucuronoxylan was measured using size exclusion chromatography with 0.05 M LiBr in DMSO:water (90:10) as the mobile phase.
  • PSS Polymer Standard Service
  • the following PSS (Polymer Standard Service) column set was used: GRAM 30, 100, 3000 (8 ⁇ 300 mm) and guard column (8 ⁇ 50 mm).
  • the flow rate was 0.4 ml/min at 60 ° C., resulting in a system pressure of 58 bar.
  • the samples were dissolved in the eluent in a shaker for 24 hours at room temperature and filtered using regenerated cellulose membranes (0.45 ⁇ m).
  • RI detector Shidex RI-71
  • Precision detectors PD 2000 Precision detectors PD 2000
  • Viscotek H502 Viscotek H502
  • the mechanical properties of the films were measured using a tensile testing machine (Lloyd L2000R) with a load cell of 100 N capacity.
  • the samples were cut into dog bone-shaped strips with a width of 1.5 cm.
  • the initial distance between the grips was 20 mm and the separation rate of the grips constant at 5 mm/min (Examples 1, 2 and 7) or 10 mm/min (Example 4). At least five replicates from each material were tested. For each sample the stress-strain curve was recorded and stress at break and strain at break were calculated.
  • the crystallinity of the films was investigated using wide angle x-ray scattering (WAXS). Films were milled to a fine powder using liquid nitrogen and the samples were investigated with a Siemens D5000 diffractometer. CuK ⁇ radiation was used with a wavelength of 1.54 ⁇ . 2 ⁇ was varied between 5° and 30°.
  • WAXS wide angle x-ray scattering
  • This example illustrates the production of a film based on xylan, where the film-forming properties have been improved using the low molecular plasticizer sorbitol.
  • the same procedure as in Example 1 was used except that sorbitol was used as plasticizer instead of xylitol and the series included three levels of plasticizers, namely 20%, 35% and 50% was investigated.
  • This example illustrates the production of films made from xylan and polyvinyl alcohol.
  • the same procedure as in Example 1 was used but 0.75 g of polyvinyl alcohol (mw 20 000) was mixed with 0.25 g of xylan. Flexible films were formed. The measured oxygen permeability of the films was 0.18 (cm 3 ⁇ m)/(m 2 d kPa).
  • This example illustrates the production of films made from xylan and finely divided cellulose.
  • the resulting gel was poured onto a polystyrene Petri dish with a diameter of 14 cm, and dried at 50° C. for 48 h. After drying a flexible film was obtained.
  • the films produced according to this method exhibited a stress at break of 102.8 MPa, a strain at break of 3.1% and an oxygen permeability of 0.225 (cm 3 ⁇ m)/(m 2 d kPa).
  • This example illustrates the production of a film based on xylan, where the xylan is obtained from an agricultural residue, such as oat spelts, barley husks or flax.
  • 1 g of arabinoxylan was solubilized in 35 ml of water in 95° C. for 15 minutes. The solution was then poured onto a polystyrene Petri dish with a diameter of 14 cm. After drying in 23° C. and 50% RH for two to three days flexible films were obtained.
  • water is the preferred plasticizer.
  • the possibility to obtain films of arabinoxylan without the addition of any other plasticizer than water is very advantageous and a surprising aspect of the present invention.
  • the thickness of the films was 30-40 ⁇ m.
  • the molar mass of the arabinoxylan was measured using size exclusion chromatography as described in example 1. The obtained molar mass was 34 000 g/mol.
  • This example illustrates the production of a coating based on xylan.
  • a mixture of 0.105 g sorbitol and 0.195 g glucoronoxylan from aspen was solubilized in 30 ml of water in 95 ° C. for 15 minutes. The solution was then poured onto a plastic film in a polystyrene Petri dish with a diameter of 14 cm. After drying in 23° C. and 50% RH for two to three days, a coating of xylan on the plastic film was obtained.
  • the molar mass of the glucuronoxylan was measured using size exclusion chromatography as described in example 1. The obtained molar mass was 15 000 g/mol.
  • the thickness of the coating was obtained by subtracting the thickness of the plastic film from the thickness of the plastic film with the xylan coating, measured using a micrometer. The obtained thickness of the coating was 1 micrometer.
  • This example illustrates the production of a film based on glucomannan, where the film-forming properties have been improved using the low molecular plasticizer sorbitol.
  • Films without sorbitol and films containing 20% of added sorbitol (dry weight) were investigated.
  • a mixture of sorbitol and glucomannan with a total weight of 0.2 g was solubilized in 20 ml of water in 95° C. for 15 minutes. The solution was then poured onto polystyrene Petri dishes with a diameter of 9 cm. After drying in 23° C. and 50% RH for two to three days, transparent and more or less flexible films were obtained.
  • the mechanical properties of the films were measured according to example 1.
  • the thickness of the samples, measured with a micrometer, was 60-70 ⁇ m.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Wrappers (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
US10/548,799 2003-03-21 2004-03-18 Polymeric film or coating comprising hemicellulose Expired - Lifetime US7427643B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
SE0300801A SE0300801D0 (sv) 2003-03-21 2003-03-21 Polymeric film or coating comprising hemicellulose
SE0300801-8 2003-03-21
PCT/SE2004/000413 WO2004083286A1 (en) 2003-03-21 2004-03-18 Polymeric film or coating comprising hemicellulose

Publications (2)

Publication Number Publication Date
US20060173104A1 US20060173104A1 (en) 2006-08-03
US7427643B2 true US7427643B2 (en) 2008-09-23

Family

ID=20290761

Family Applications (1)

Application Number Title Priority Date Filing Date
US10/548,799 Expired - Lifetime US7427643B2 (en) 2003-03-21 2004-03-18 Polymeric film or coating comprising hemicellulose

Country Status (15)

Country Link
US (1) US7427643B2 (de)
EP (1) EP1606339B2 (de)
JP (1) JP4604023B2 (de)
CN (1) CN100335532C (de)
AT (1) ATE402216T2 (de)
AU (1) AU2004221959B2 (de)
BR (1) BRPI0408511B1 (de)
CA (1) CA2516612C (de)
DE (1) DE602004015263D1 (de)
DK (1) DK1606339T4 (de)
ES (1) ES2310723T5 (de)
PL (1) PL1606339T5 (de)
PT (1) PT1606339E (de)
SE (1) SE0300801D0 (de)
WO (1) WO2004083286A1 (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012109357A2 (en) * 2011-02-08 2012-08-16 Advanced Polymer Technology Ab Plasticizer-free flexible oxygen barrier films and laminates based on negatively charged and acetylated non-cellulosic polysaccharides isolated from biomass
US20140065406A1 (en) * 2011-05-04 2014-03-06 Kth Holding Ab Oxygen barrier for packaging applications
US20150232582A1 (en) * 2014-02-19 2015-08-20 Celanese Acetate Llc Hemicellulose Compositions
US10612059B2 (en) 2015-04-10 2020-04-07 Comet Biorefining Inc. Methods and compositions for the treatment of cellulosic biomass and products produced thereby
US10633461B2 (en) 2018-05-10 2020-04-28 Comet Biorefining Inc. Compositions comprising glucose and hemicellulose and their use
WO2024157029A1 (en) 2023-01-26 2024-08-02 Sun Chemical B.V. Dehazing coatings and method for use

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060029671A1 (en) * 2004-08-06 2006-02-09 Grain Processing Corporation Tablet coating composition
NO20065147L (no) * 2006-11-08 2008-05-09 Ntnu Tech Transfer As Nanokompositter basert på cellulosewhiskers og celluloseplast
SE0700404L (sv) * 2007-02-19 2008-08-20 Xylophane Ab Polymerfilm eller -beläggning innefattande hemicellulosa
FI121811B (fi) * 2007-06-01 2011-04-29 Upm Kymmene Corp Uudet dispersiot ja menetelmä niiden valmistamiseksi
DE602007008591D1 (de) † 2007-11-27 2010-09-30 Innventia Ab Verwendung eines Holzhydrolysats
EP2247652A1 (de) 2008-02-22 2010-11-10 Basf Se Verfahren zur herstellung fester materialien auf der basis von synthetischen polymeren und/oder biopolymeren und ihre verwendung
US8772406B2 (en) * 2009-08-06 2014-07-08 Robert J. Linhardt Synthetic wood composite
SE1250261A1 (sv) * 2011-10-31 2013-05-01 Billerudkorsnaes Gaevle Froevi Ab Bestrykningskomposition, ett förfarande för bestrykning av ett substrat, ettbestruket substrat, ett förpackningsmaterial och vätskeförpackning
WO2013066246A1 (en) * 2011-10-31 2013-05-10 Xylophane Aktiebolag Migration barrier film or coating comprising hemicellulose
CN102775647B (zh) * 2012-07-30 2014-07-30 昆明理工大学 一种半纤维素基可食膜的制备方法
JP6043693B2 (ja) * 2012-10-19 2016-12-14 富士フイルム株式会社 保護膜形成用の樹脂組成物、保護膜、パターン形成方法、電子デバイスの製造方法及び電子デバイス
CN103382677B (zh) * 2013-07-25 2015-11-04 海南必凯水性涂料有限公司 一种用于内衬纸涂布的高阻隔聚乙烯醇涂料及其制备方法
DE102016201498B4 (de) 2016-02-01 2017-08-17 Norbert Kuhl Sauerstoffdichter lebensmittelbehälter
CN106497085A (zh) * 2016-11-03 2017-03-15 金福英 一种可食性包装薄膜及其制备方法
DE102017211562B4 (de) * 2017-07-06 2021-12-02 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Beschichtete Cellulosefaser, Verfahren zu deren Herstellung, faserverstärkter Verbundwerkstoff, Verfahren zu dessen Herstellung und dessen Verwendung
CN110078883B (zh) * 2019-05-22 2021-08-03 西华大学 一种基于魔芋粉的水性涂料树脂、其制备方法与组合物
SE544369C2 (en) * 2020-06-30 2022-04-26 Stora Enso Oyj Barrier Coating for Paper and Paperboard
SE545615C2 (en) * 2021-06-09 2023-11-14 Stora Enso Oyj Barrier coating comprising a first and a second polysaccharide for paper and paperboard, coated substrate and method for the production thereof
CN115466414B (zh) * 2022-01-25 2023-08-01 北京林业大学 一种半纤维素基塑料的制备方法

Citations (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4419316A (en) * 1974-07-10 1983-12-06 Schweiger Richard Georg Process of making films, fibers or other shaped articles consisting of, or containing, polyhydroxy polymers
US4506044A (en) * 1979-07-10 1985-03-19 Lever Brothers Company Microbial heteropolysaccharide
US4564649A (en) * 1984-04-16 1986-01-14 H. B. Fuller Company Polyvinyl alcohol and lignin sulfonate containing adhesive
US4725657A (en) * 1984-12-27 1988-02-16 Japan Liquid Crystal Co., Ltd. Synthetic resin product containing compound included in cyclodextrin and process for the production of the same
EP0400484A1 (de) 1989-05-23 1990-12-05 Mitsubishi Rayon Co., Ltd Essbare Folie und Verfahren zu deren Herstellung
US5095054A (en) * 1988-02-03 1992-03-10 Warner-Lambert Company Polymer compositions containing destructurized starch
JPH04331246A (ja) 1991-04-10 1992-11-19 Goyo Paper Working Co Ltd ガスバリヤー性材料及び該材料を用いた容器用基材
US5179021A (en) * 1989-02-10 1993-01-12 Gil Inc. (Now Ici Canada Inc.) Pulp bleaching process comprising oxygen delignification and xylanase enzyme treatment
EP0612789A1 (de) 1993-02-26 1994-08-31 SORGHO AGRO-INDUSTRIEL ET PAPETIER S.A.I.S. Société Anonyme Verfahren zur Herstellung von weichen, festen und biologisch abbaubaren Folien und erhaltene Produkte
US5468287A (en) 1992-11-02 1995-11-21 Fuji Oil Co., Ltd. Water color
FR2730236A1 (fr) 1995-02-08 1996-08-09 Generale Sucriere Sa Procede de valorisation de pulpes de betterave, en particulier pour preparer des colles, des produits d'enduction, ou des films adhesifs reversibles a l'eau
US5646206A (en) * 1993-04-23 1997-07-08 The United States Of America As Represented By The Secretary Of Agriculture Films fabricated from mixtures of pectin and poly(vinyl alchohol)
US5800602A (en) * 1995-05-10 1998-09-01 Hoechst Aktiengesellschaft Use of inclusion compounds of cyclic polysaccharides as charge control agents
US5981790A (en) 1994-12-14 1999-11-09 Rhone-Poulenc Fiber And Resin Intermediates Method for partially hydrogenating dinitriles to aminonitriles
US6004616A (en) 1990-02-07 1999-12-21 Fuji Oil Company, Ltd. Biodegradable vegetable film
US6057438A (en) * 1996-10-11 2000-05-02 Eastman Chemical Company Process for the co-production of dissolving-grade pulp and xylan
EP1095977A1 (de) 1999-10-28 2001-05-02 Ucb, S.A. Wässrige Polymerzusammensetzung mit einem Biopolymer und einem Polymerharz
US6261578B1 (en) * 1998-06-15 2001-07-17 L'oreal Cosmetic composition containing a polysaccharide and an acrylic terpolymer, and use of this composition for the treatment of keratinous material
US20010020091A1 (en) * 1999-02-10 2001-09-06 Eastman Chemical Company Corn fiber for the production of advanced chemicals and materials: arabinoxylan and arabinoxylan derivatives prepared therefrom
WO2001068713A2 (en) * 2000-03-16 2001-09-20 Sca Hygiene Products Ab Polysaccharide - based superabsorbent film
WO2002006411A1 (fr) 2000-07-18 2002-01-24 Ulice (Unite De Laboratoire Pour L'innovation Dans Les Cereales) Utilisation d'heteroxylanes pour la preparation de compositions filmogenes
US6362256B2 (en) * 1999-04-12 2002-03-26 The United States Of America As Represented By The Secretary Of Agriculture Biodegradable polymer compositions, methods for making same and articles therefrom
US6395204B1 (en) * 2000-01-28 2002-05-28 Weyerhaeuser Company Plastic wood, method of processing plastic wood, and resulting products
US20020107303A1 (en) * 2000-10-12 2002-08-08 Seiko Epson Corporation Method of preparation of polymer emulsion and ink composition comprising the polymer emulsion
WO2002079332A1 (en) * 2001-03-28 2002-10-10 Polysaccharide Industries Ab Protective coating
US20020188041A1 (en) * 2001-05-10 2002-12-12 Bond Eric Bryan Fibers comprising starch and biodegradable polymers
US6558728B1 (en) * 1996-05-10 2003-05-06 Danisco A/S α-glucuronidases of aspergillus, production thereof and their uses
US20030171458A1 (en) * 2002-01-16 2003-09-11 Buchanan Charles M. Novel carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same
US20040129395A1 (en) * 2002-10-01 2004-07-08 The Procter & Gamble Company Strengthened tissue paper products comprising low levels of xylan
US6878760B2 (en) * 2001-09-14 2005-04-12 The Goodyear Tire & Rubber Company Preparation of starch reinforced rubber and use thereof in tires
US20060051812A1 (en) * 2002-10-04 2006-03-09 Glykos Finland Oy Novel carbohydrate compositions and a process of preparing same
US20060235115A1 (en) * 2003-05-06 2006-10-19 The United States Of America, As Represented By The Secretary Of Agriculture Wood adhesives containing solid residues of biomass fermentations
US20070179218A1 (en) * 2006-01-27 2007-08-02 Jeffrey Brake Blends of biopolymers with acrylic copolymers

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1119932C (zh) * 2000-07-07 2003-09-03 中国科学院生态环境研究中心 生物种衣剂
FR2829142B1 (fr) * 2001-12-27 2004-02-13 Ulice Composition filmogene d'heteroxylanes pour la fabrication de capsules ainsi obtenues
DE10208858A1 (de) * 2002-03-01 2003-09-11 Kalle Gmbh & Co Kg Rauch- und wasserdampfdurchlässige Nahrungsmittelhülle aus einem thermoplastischen Gemisch

Patent Citations (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4419316A (en) * 1974-07-10 1983-12-06 Schweiger Richard Georg Process of making films, fibers or other shaped articles consisting of, or containing, polyhydroxy polymers
US4506044A (en) * 1979-07-10 1985-03-19 Lever Brothers Company Microbial heteropolysaccharide
US4564649A (en) * 1984-04-16 1986-01-14 H. B. Fuller Company Polyvinyl alcohol and lignin sulfonate containing adhesive
US4725657A (en) * 1984-12-27 1988-02-16 Japan Liquid Crystal Co., Ltd. Synthetic resin product containing compound included in cyclodextrin and process for the production of the same
US5095054A (en) * 1988-02-03 1992-03-10 Warner-Lambert Company Polymer compositions containing destructurized starch
US5179021A (en) * 1989-02-10 1993-01-12 Gil Inc. (Now Ici Canada Inc.) Pulp bleaching process comprising oxygen delignification and xylanase enzyme treatment
EP0400484A1 (de) 1989-05-23 1990-12-05 Mitsubishi Rayon Co., Ltd Essbare Folie und Verfahren zu deren Herstellung
US20030021865A1 (en) * 1990-02-07 2003-01-30 Hirokazu Maeda Process for production of water-soluble vegetable fibers, biodegradable film, paste, chewing gum and low calorie food products
US6004616A (en) 1990-02-07 1999-12-21 Fuji Oil Company, Ltd. Biodegradable vegetable film
JPH04331246A (ja) 1991-04-10 1992-11-19 Goyo Paper Working Co Ltd ガスバリヤー性材料及び該材料を用いた容器用基材
US5468287A (en) 1992-11-02 1995-11-21 Fuji Oil Co., Ltd. Water color
EP0612789A1 (de) 1993-02-26 1994-08-31 SORGHO AGRO-INDUSTRIEL ET PAPETIER S.A.I.S. Société Anonyme Verfahren zur Herstellung von weichen, festen und biologisch abbaubaren Folien und erhaltene Produkte
US5646206A (en) * 1993-04-23 1997-07-08 The United States Of America As Represented By The Secretary Of Agriculture Films fabricated from mixtures of pectin and poly(vinyl alchohol)
US5981790A (en) 1994-12-14 1999-11-09 Rhone-Poulenc Fiber And Resin Intermediates Method for partially hydrogenating dinitriles to aminonitriles
FR2730236A1 (fr) 1995-02-08 1996-08-09 Generale Sucriere Sa Procede de valorisation de pulpes de betterave, en particulier pour preparer des colles, des produits d'enduction, ou des films adhesifs reversibles a l'eau
US5800602A (en) * 1995-05-10 1998-09-01 Hoechst Aktiengesellschaft Use of inclusion compounds of cyclic polysaccharides as charge control agents
US6558728B1 (en) * 1996-05-10 2003-05-06 Danisco A/S α-glucuronidases of aspergillus, production thereof and their uses
US6057438A (en) * 1996-10-11 2000-05-02 Eastman Chemical Company Process for the co-production of dissolving-grade pulp and xylan
US6261578B1 (en) * 1998-06-15 2001-07-17 L'oreal Cosmetic composition containing a polysaccharide and an acrylic terpolymer, and use of this composition for the treatment of keratinous material
US20010020091A1 (en) * 1999-02-10 2001-09-06 Eastman Chemical Company Corn fiber for the production of advanced chemicals and materials: arabinoxylan and arabinoxylan derivatives prepared therefrom
US6362256B2 (en) * 1999-04-12 2002-03-26 The United States Of America As Represented By The Secretary Of Agriculture Biodegradable polymer compositions, methods for making same and articles therefrom
EP1095977A1 (de) 1999-10-28 2001-05-02 Ucb, S.A. Wässrige Polymerzusammensetzung mit einem Biopolymer und einem Polymerharz
US6395204B1 (en) * 2000-01-28 2002-05-28 Weyerhaeuser Company Plastic wood, method of processing plastic wood, and resulting products
WO2001068713A2 (en) * 2000-03-16 2001-09-20 Sca Hygiene Products Ab Polysaccharide - based superabsorbent film
WO2002006411A1 (fr) 2000-07-18 2002-01-24 Ulice (Unite De Laboratoire Pour L'innovation Dans Les Cereales) Utilisation d'heteroxylanes pour la preparation de compositions filmogenes
US20020107303A1 (en) * 2000-10-12 2002-08-08 Seiko Epson Corporation Method of preparation of polymer emulsion and ink composition comprising the polymer emulsion
WO2002079332A1 (en) * 2001-03-28 2002-10-10 Polysaccharide Industries Ab Protective coating
US20020188041A1 (en) * 2001-05-10 2002-12-12 Bond Eric Bryan Fibers comprising starch and biodegradable polymers
US6878760B2 (en) * 2001-09-14 2005-04-12 The Goodyear Tire & Rubber Company Preparation of starch reinforced rubber and use thereof in tires
US20030171458A1 (en) * 2002-01-16 2003-09-11 Buchanan Charles M. Novel carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same
US20040129395A1 (en) * 2002-10-01 2004-07-08 The Procter & Gamble Company Strengthened tissue paper products comprising low levels of xylan
US20060051812A1 (en) * 2002-10-04 2006-03-09 Glykos Finland Oy Novel carbohydrate compositions and a process of preparing same
US20060235115A1 (en) * 2003-05-06 2006-10-19 The United States Of America, As Represented By The Secretary Of Agriculture Wood adhesives containing solid residues of biomass fermentations
US20070179218A1 (en) * 2006-01-27 2007-08-02 Jeffrey Brake Blends of biopolymers with acrylic copolymers

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
"An industry rule-of-thumb is that a material is considered a "high oxygen barrier" if its OTR is less than 1 cc/100 in2/24hr (15.5 cc/m2/24 hr)." http://www.polyprint.com/faq<SUB>-</SUB>otr.htm.
"Certain polymers are particularly useful in restricting entry of oxygen into packages. Such polymers, because they are highly impermeable to oxygen, are called high barrier polymers. They typically have an oxygen transmission rate (OTR) at 20� C of less than 15 cc/m2-day atm." http://www.intracen.org/Tdc/Export%20packaging/EPN/English/epn38e.pdf.
Ackermann, P., J�gerstad, M., & Ohlsson, T. (Eds.). (1995). Foods and Packaging Materials-Chemical Interactions. Lund: The Royal Society of Chemistry.
Bain, D. R., & Giles, G. A. (Red.). (2000). Materials and Development of Plastic Packaging for the Consumer Market. England: Sheffield Academic Press.
Indian Office Action issued in Indian counterpart application on Dec. 9, 2006.
McHugh, T. H.; Krochta, J. M. Permeability properties of edible films. In Edible Coatings and Films to Improve Food Quality; Krochta, J. M.; Baldwin, E. A.; Nisperos-Carriedo, M. O., Eds.; Technomic Publishing Company: Lancaster (1994); pp. 139-187.
p. 137 in Foods and Packaging Materials-Chemical Interactions, 1995.
p. 23 in Piringer & Baner, 2000.
p. 25 in Robertsson, 2006.
p. 30 in Bain & Giles, 2000.
p. 4-5: http://akseli.tekes.fi/opencms/opencms/OhjelmaPortaali/ohjelmat/Pakkaus/fi/Dokumenttiarkisto/Viestinta<SUB>-</SUB>ja<SUB>-</SUB>aktivointi/Seminaarit/seminaari<SUB>-</SUB>6.10.2004/SIP<SUB>-</SUB>Rolig.pdf.
Piringer, O. -G., & Baner, A. L. (Red.). (2000). Plastic Packaging Materials for Food-barrier function, mass transport, qualtity assurance, and legislation. Germany: Wiley-vch Verlag.
Rindlav-Westling, �.; Stading, M.; Hermansson, A.-M.; Gatenholm, P. Structure, mechanical and barrier properties of amylose and amylopectin films. Carbohydrate Polymers (1998), 36, 217-224.
Robertsson, G. L. (2006). Food Packaging-Principles and Practice (Second Edition uppl.). CRC Press.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012109357A2 (en) * 2011-02-08 2012-08-16 Advanced Polymer Technology Ab Plasticizer-free flexible oxygen barrier films and laminates based on negatively charged and acetylated non-cellulosic polysaccharides isolated from biomass
WO2012109357A3 (en) * 2011-02-08 2012-10-26 Advanced Polymer Technology Ab Plasticizer-free flexible oxygen barrier films and laminates based on negatively charged and acetylated non-cellulosic polysaccharides isolated from biomass
US9637561B2 (en) 2011-02-08 2017-05-02 Advanced Polymer Technology Ab Plasticizer-free flexible oxygen barrier films and laminates based on negatively charged and acetylated non-cellulosic polysaccharides isolated from biomass
US20140065406A1 (en) * 2011-05-04 2014-03-06 Kth Holding Ab Oxygen barrier for packaging applications
US20150232582A1 (en) * 2014-02-19 2015-08-20 Celanese Acetate Llc Hemicellulose Compositions
US10612059B2 (en) 2015-04-10 2020-04-07 Comet Biorefining Inc. Methods and compositions for the treatment of cellulosic biomass and products produced thereby
US11692211B2 (en) 2015-04-10 2023-07-04 Comet Biorefining Inc. Methods and compositions for the treatment of cellulosic biomass and products produced thereby
US10633461B2 (en) 2018-05-10 2020-04-28 Comet Biorefining Inc. Compositions comprising glucose and hemicellulose and their use
US11525016B2 (en) 2018-05-10 2022-12-13 Comet Biorefining Inc. Compositions comprising glucose and hemicellulose and their use
WO2024157029A1 (en) 2023-01-26 2024-08-02 Sun Chemical B.V. Dehazing coatings and method for use

Also Published As

Publication number Publication date
PT1606339E (pt) 2008-10-22
CA2516612C (en) 2012-06-26
CN1761703A (zh) 2006-04-19
DK1606339T3 (da) 2008-10-20
BRPI0408511B1 (pt) 2016-03-22
AU2004221959A1 (en) 2004-09-30
EP1606339A1 (de) 2005-12-21
ATE402216T2 (de) 2008-08-15
PL1606339T3 (pl) 2008-12-31
DE602004015263D1 (de) 2008-09-04
PL1606339T5 (pl) 2017-12-29
BRPI0408511A (pt) 2006-03-07
CN100335532C (zh) 2007-09-05
WO2004083286A1 (en) 2004-09-30
SE0300801D0 (sv) 2003-03-21
ES2310723T3 (es) 2009-01-16
EP1606339B1 (de) 2008-07-23
ES2310723T5 (es) 2017-07-12
DK1606339T4 (en) 2017-05-01
AU2004221959B2 (en) 2009-03-26
US20060173104A1 (en) 2006-08-03
JP2006520843A (ja) 2006-09-14
CA2516612A1 (en) 2004-09-30
EP1606339B2 (de) 2017-04-26
JP4604023B2 (ja) 2010-12-22

Similar Documents

Publication Publication Date Title
US7427643B2 (en) Polymeric film or coating comprising hemicellulose
EP2754703B1 (de) Polymerform oder schicht mit Hemicellulose
Chen et al. Preparation and performance of thermoplastic starch and microcrystalline cellulose for packaging composites: Extrusion and hot pressing
Zhang et al. Functional packaging films originating from hemicelluloses laurate by direct transesterification in ionic liquid
Jain et al. Thermoplastic xylan derivatives with propylene oxide
DE69634214T2 (de) Zusammensetzungen von hydroxyfunktionellen Polymeren
Oinonen et al. Bioinspired composites from cross-linked galactoglucomannan and microfibrillated cellulose: Thermal, mechanical and oxygen barrier properties
Zhang et al. Synergistic effects of graft polymerization and polymer blending on the flexibility of xylan-based films
Karaaslan et al. Semi‐interpenetrating polymer network hydrogels based on aspen hemicellulose and chitosan: Effect of crosslinking sequence on hydrogel properties
Chen et al. Influence of ammonium zirconium carbonate on properties of poly (vinyl alcohol)/xylan composite films
Heikkinen et al. Long-Term Physical Stability of Plasticized Hemicellulose Films.
Briones et al. Liquefaction of corn husks and properties of biodegradable biopolyol blends
EP2483335B1 (de) Xyloglucanfolien
Missio et al. Exploring tannin extracts: Introduction to new bio-based materials
Fabunmi et al. Effects of incorporating polycaprolactone and flax fiber into glycerol-plasticized pea starch
US20240301151A1 (en) A film material
Bonilla et al. EFFECT OF THE INCORPORATION OF ANTIOXIDANTS ON THE PROPERTIES OF WHEAT STARCH-CHITOSAN FILMS
Erdemir Effects of hemicellulose extraction and extrusion parameters on the properties of hemicellulose based polymeric materials obtained from different lignocellulosic biomass

Legal Events

Date Code Title Description
AS Assignment

Owner name: XYLOPHANE AKTIEBOLAG, SWEDEN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:GATENHOLM, PAUL;GRONDAHL, MARIA;ERICKSSON, LISA;AND OTHERS;REEL/FRAME:016595/0073;SIGNING DATES FROM 20050823 TO 20050829

STCF Information on status: patent grant

Free format text: PATENTED CASE

AS Assignment

Owner name: XYLOPHANE AB, SWEDEN

Free format text: CHANGE OF ADDRESS;ASSIGNOR:XYLOPHANE AB;REEL/FRAME:025433/0990

Effective date: 20101101

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

AS Assignment

Owner name: SEELUTION AB, SWEDEN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:XYLOPHANE AB;REEL/FRAME:041425/0755

Effective date: 20170217

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 12TH YR, SMALL ENTITY (ORIGINAL EVENT CODE: M2553); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY

Year of fee payment: 12